Sodium borohydride → HCID 15096976, compound

HRID 846732Notes

Reaction equation

HRID 846732 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][CH:9]([OH:11])[CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15096993HCID 15096993, compound

Product 1

HCID 15096976HCID 15096976, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 37.6 parts of 4-(4-fluorophenoxy)-2-butanone and 400 parts of ethanol were added portionwise 21.2 parts of sodium borohydride at a temperature below 20° C. Upon completion, stirring was continued for 1 hour at room temperature. The reaction mixture was concentrated to half its volume. After cooling, 500 parts of water were added and evaporation was continued till all ethanol was removed. After cooling, the product was extracted with 1,1'-oxybisethane. The extract was washed with water, dried, filtered and evaporated. The oily residue was distilled, yielding 20.80 parts (55.1%) of 4-(4-fluorophenoxy)-2-butanol; bp. 140°-141° C. (water-jet) (intermediate 27).

Workup

  1. concentrationThe reaction mixture was concentrated to half its volume
  2. temperatureAfter cooling
  3. addition500 parts of water were added
  4. customevaporation
  5. customwas removed
  6. temperatureAfter cooling
  7. extractionthe product was extracted with 1,1'-oxybisethane
  8. washThe extract was washed with water
  9. customdried
  10. filtrationfiltered
  11. customevaporated
  12. distillationThe oily residue was distilled

Sources & evidence

ORD record
ord-a0ebeab21eda4407aa3dbfae09f1877f
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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